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Search term: CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O (Found by conversion of search term to chemical structure (full match))
ChemSpider 2D Image | Embelin | C17H26O4

Embelin

  • Molecular FormulaC17H26O4
  • Average mass294.386 Da
  • Monoisotopic mass294.183105 Da
  • ChemSpider ID3105

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl- [ACD/Index Name]
2,5-Dihydroxy-3-undecyl-1,4-benzochinon [German] [ACD/IUPAC Name]
2,5-Dihydroxy-3-undecyl-1,4-benzoquinone [ACD/IUPAC Name]
2,5-Dihydroxy-3-undécyl-1,4-benzoquinone [French] [ACD/IUPAC Name]
2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
208-979-8 [EINECS]
550-24-3 [RN]
Embelic acid
Embelin
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

SHC6U8F5ER [DBID]
AIDS009914 [DBID]
AIDS-009914 [DBID]
BRN 1885786 [DBID]
BSPBio_003531 [DBID]
DivK1c_006597 [DBID]
DK4230000 [DBID]
E1406_SIGMA [DBID]
Embelic acid;Emberine;NSC 91874 [DBID]
embelin;nsc91874 [DBID]
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  • Experimental Physico-chemical Properties
  • Predicted Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from <ital>Lysimachia punctata</ital> and < ital>Embelia ribes</ital>, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease. ChEBI CHEBI:4778
      A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4778, CHEBI:4778

    • Bio Activity:

      Apoptosis Tocris Bioscience 2156
      Apoptosis MedChem Express HY-17473
      Apoptosis; MedChem Express HY-17473
      Cell Biology Tocris Bioscience 2156
      Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 ?M in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction wi th caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC50 4 - 6 ?M), but has a weaker effect on normal prostate cells (IC50 = 19 - 20 ?M). O vercomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo. Tocris Bioscience 2156
      Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 ?M in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC50 4 - 6 ?M), but has a weaker effect on normal prostate cells (IC50 = 19 - 20 ?M). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo. Tocris Bioscience 2156
      Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 muM in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC50 4 - 6 muM), but has a weaker effect on normal prostate cells (IC50 = 19 - 20 muM). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo. Tocris Bioscience 2156
      Embelin is a cell-permeable benzoquinone compound that exhibits antitumor properties. MedChem Express http://www.medchemexpress.com/azilsartan-medoxomil-monopotassium.html, HY-17473
      Embelin is a cell-permeable benzoquinone compound that exhibits antitumor properties. Specifically antagonizes XIAP-mediated inhibition of caspase-9 activation by directly targeting the Smac and caspase-9 binding domain BIR3 (IC50 = 4.1 uM in a competitive binding assay with Smac peptide).;IC50 value: 4.1 uM [1];Target: XIAP;In vitro: Embelin induced activation of caspase-9 and embelin-induced apoptosis was prevented by caspase inhibitors [2]. Treatment with subtoxic doses of Embelin broadly sensitized malignant glioma cells to TRAIL-mediated apoptosis. Notably, human astrocytes were not significantly affected by the combined treatment consisting of Embelin and TRAIL. Combined treatment with Embelin and TRAIL augmented the activation of initiator caspases-8/-9 and effector caspases-3/-7, respectively [3]. ;In vivo: Embelin inhibited topical edema in the mouse ear, leading to substantial reductions in skin thickness and tissue weight, inflammatory cytokine production, neutrophil-m MedChem Express HY-17473
      IAP MedChem Express HY-17473
      Inhibitor of Apoptosis (IAP) Tocris Bioscience 2156
      Inhibitor of X-linked inhibitor of apoptosis (XIAP); cell-permeable and antitumor Tocris Bioscience 2156

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.1±0.1 g/cm3
Boiling Point: 431.9±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 79.4±6.0 kJ/mol
Flash Point: 229.1±25.2 °C
Index of Refraction: 1.538
Molar Refractivity: 81.3±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 1
ACD/LogP: 5.70
ACD/LogD (pH 5.5): 1.06
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.38
ACD/LogD (pH 7.4): 0.54
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 75 Å2
Polarizability: 32.2±0.5 10-24cm3
Surface Tension: 49.5±3.0 dyne/cm
Molar Volume: 260.1±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.34

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  477.63  (Adapted Stein & Brown method)
    Melting Pt (deg C):  195.58  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.98E-011  (Modified Grain method)
    MP  (exp database):  142.5 deg C
    Subcooled liquid VP: 3.06E-010 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  2.599
       log Kow used: 4.34 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.00015815 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Quinone/Hydroquinone
       Vinyl/Allyl Alcohols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.98E-005  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.951E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.34  (KowWin est)
  Log Kaw used:  -2.691  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.031
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.0469
   Biowin2 (Non-Linear Model)     :   0.8810
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.1219  (weeks       )
   Biowin4 (Primary Survey Model) :   3.9065  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.8948
   Biowin6 (MITI Non-Linear Model):   0.8854
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.1069
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  4.08E-008 Pa (3.06E-010 mm Hg)
  Log Koa (Koawin est  ): 7.031
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  73.5 
       Octanol/air (Koa) model:  2.64E-006 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.000211 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  38.1696 E-12 cm3/molecule-sec
      Half-Life =     0.280 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.363 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.312500 E-17 cm3/molecule-sec
      Half-Life =     0.873 Days (at 7E11 mol/cm3)
      Half-Life =     20.955 Hrs
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.642 (BCF = 43.88)
       log Kow used: 4.34 (estimated)

 Volatilization from Water:
    Henry LC:  4.98E-005 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      21.92  hours
    Half-Life from Model Lake :        383  hours   (15.96 days)

 Removal In Wastewater Treatment:
    Total removal:              48.37  percent
    Total biodegradation:        0.45  percent
    Total sludge adsorption:    46.60  percent
    Total to Air:                1.32  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.399           5.09         1000       
   Water     18.7            360          1000       
   Soil      75.9            720          1000       
   Sediment  5.02            3.24e+003    0          
     Persistence Time: 534 hr

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